Water → HCID 9794121, compound

HRID 586112Notes

Reaction equation

HRID 586112 reaction equation
O.[CH2:2]([N:9]1[CH2:12][CH2:11][CH:10]1[C:13]([O:15]CC)=[O:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CC(CC(C)C)=O>C(O)C>[CH2:2]([N:9]1[CH2:12][CH2:11][C@H:10]1[C:13]([OH:15])=[O:14])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7909Methyl Isobutyl KetoneHCID 11074886Ethyl 1-benzylazetidine-2-carboxylate

Product 1

HCID 9794121HCID 9794121, compoundYield 105.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

To 77 g of water were added 0.5 g of the immobilized enzyme produced in Example 1 above and 65 g of ethyl N-benzylazetidine-2-carboxylate, followed by stirring at 10° C. for 10 hours. To the reaction mixture, were added 65 g of methylisobutyl ketone and 36 g of ethanol, and further stirring was conducted for 30 minutes. The reaction mixture was thereafter filtrated, and the filtrate was subjected to separation. To the aqueous layer were added 65 g of methylisobutyl ketone and 6.5 g of ethanol followed by stirring for 30 minutes and the separation. This operation was repeated twice. Thus resulting aqueous layer was concentrated under a reduced pressure (10 kPa or lower) to give 60 g of crude (S)-N-benzylazetidine-2-carboxylic acid (43 weight %).

Workup

  1. customproduced in Example 1 above
  2. stirringfurther stirring
  3. waitwas conducted for 30 minutes
  4. filtrationThe reaction mixture was thereafter filtrated
  5. customthe filtrate was subjected to separation
  6. additionTo the aqueous layer were added 65 g of methylisobutyl ketone and 6.5 g of ethanol
  7. stirringby stirring for 30 minutes
  8. customthe separation
  9. concentrationThus resulting aqueous layer was concentrated under a reduced pressure (10 kPa or lower)

Sources & evidence

ORD record
ord-a524d65c57004a35af097125db9a7381
Source dataset
uspto-grants-2005_08
Patent number
US06936445B2

Reaction notes

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